(2R,4S)-2,4-pentanediol | 157840-12-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,4S)-2,4-pentanediol
• 英文别名: [(2R,4S)-4-ethenoxypentan-2-yl]oxybenzene
• CAS: 157840-12-5
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: GWNJAQUUHVGZAC-NWDGAFQWSA-N

物化性质

• 沸点：
  288.1±23.0 °C(Predicted)
• 密度：
  0.960±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,4S)-2,4-pentanediol 以 正戊烷 为溶剂， 反应 4.0h， 以70%的产率得到
  参考文献：
  名称：

  Stereocontrolled intramolecular meta-arene–alkene photocycloaddition reactions using chiral tethers: efficiency of the tether derived from 2,4-pentanediol

  摘要：

  Photochemical reactions of substrates consisting of phenyl and vinyl groups, which are tethered with a chiral diol, resulted in intramolecular meta-arene-alkene cycloaddition; the reaction efficiency as well as the stereoselectivity was studied. 1,3-Butanediol, 2-substituted 1,3-propanediols, 2-methyl-2,4-penetanediol, and 2,6-dimethyl-3,5-heptanediol were employed as tethers, and the results are compared with those obtained with 2,4-pentanediol (PD) tether, which are known to show high stereoselectivity and moderate efficiency. All the reactions with the lower analogues were less efficient than with PD, although one of the butanediol-tethered reactions afforded a single stereoisomer as PD did. The dimethylheptanediol tether showed similar efficiency but lower stereoselectivity than PD. The results suggest that the PD tether has an optimized structure having a proper flexibility. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.086
• 作为产物：
  描述：

  (2R,4R)-4-苯氧基-2-戊醇 在 sodium hydroxide 、 mercury(II) diacetate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 水 为溶剂， 反应 23.0h， 生成 (2R,4S)-2,4-pentanediol
  参考文献：
  名称：

  Asymmetric meta-arene–alkene photocycloaddition controlled by a 2,4-pentanediol tether

  摘要：

  Photo-irradiation of a substrate having phenyl and vinyl groups resulted in a stereocontrolled meta-arene-alkene cycloaddition when the two groups were connected by a chiral 2,4-pentanediol tether. The regioselectivity during the ring closing step after the initial addition was dependent on the stereochemistry of the tether and the photolysis conditions. The substrate bearing a p-tolyl or 3,5-xylyl group instead of the phenyl also underwent strict stereocontrolled addition. In the case of the o- and m-tolyl substrates, the regioselectivity due to the unsymmetric substitution of the arene moiety was also fully controlled. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.03.017

文献信息

• Regio- and diastereo-chemically controlled photocycloaddition of an arene and an alkene linked by a chiral auxiliary
  作者：Takashi Sugimura、Norio Nishiyama、Akira Tai、Tadao Hakushi

  DOI：10.1016/0957-4166(94)80147-9

  日期：1994.7

  Intramolecular meta-arene-alkene photocycloaddition of 1b, the substrate having a chiral auxiliary as a linking bridge between the arene and the alkene, resulted in high diastereofacial differentiation of the alkene at the addition step and sufficient regiocontrol of the subsequent ring closure step to give a single diastereomer 4.
• Asymmetric meta-arene–alkene photocycloaddition controlled by a 2,4-pentanediol tether
  作者：Kazutake Hagiya、Akiko Yamasaki、Tadashi Okuyama、Takashi Sugimura

  DOI：10.1016/j.tetasy.2004.03.017

  日期：2004.5

  Photo-irradiation of a substrate having phenyl and vinyl groups resulted in a stereocontrolled meta-arene-alkene cycloaddition when the two groups were connected by a chiral 2,4-pentanediol tether. The regioselectivity during the ring closing step after the initial addition was dependent on the stereochemistry of the tether and the photolysis conditions. The substrate bearing a p-tolyl or 3,5-xylyl group instead of the phenyl also underwent strict stereocontrolled addition. In the case of the o- and m-tolyl substrates, the regioselectivity due to the unsymmetric substitution of the arene moiety was also fully controlled. (C) 2004 Elsevier Ltd. All rights reserved.
• Stereocontrolled intramolecular meta-arene–alkene photocycloaddition reactions using chiral tethers: efficiency of the tether derived from 2,4-pentanediol
  作者：Takashi Sugimura、Akiko Yamasaki、Tadashi Okuyama

  DOI：10.1016/j.tetasy.2004.11.086

  日期：2005.2

  Photochemical reactions of substrates consisting of phenyl and vinyl groups, which are tethered with a chiral diol, resulted in intramolecular meta-arene-alkene cycloaddition; the reaction efficiency as well as the stereoselectivity was studied. 1,3-Butanediol, 2-substituted 1,3-propanediols, 2-methyl-2,4-penetanediol, and 2,6-dimethyl-3,5-heptanediol were employed as tethers, and the results are compared with those obtained with 2,4-pentanediol (PD) tether, which are known to show high stereoselectivity and moderate efficiency. All the reactions with the lower analogues were less efficient than with PD, although one of the butanediol-tethered reactions afforded a single stereoisomer as PD did. The dimethylheptanediol tether showed similar efficiency but lower stereoselectivity than PD. The results suggest that the PD tether has an optimized structure having a proper flexibility. (C) 2004 Elsevier Ltd. All rights reserved.